Methylamine → HCID 12800950, compound

HRID 1448043Notes

Reaction equation

HRID 1448043 reaction equation
[CH3:1][C:2]1([CH:15]2[CH2:19][CH2:18][O:17][C:16]2=[O:20])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[CH3:21][NH2:22]>O1CCCC1.[Cl-].[Na+].O>[CH3:21][NH:22][C:16](=[O:20])[CH:15]([CH2:19][CH2:18][OH:17])[C:2]1([CH3:1])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 2

HCID 6329MethylamineHCID 12507637HCID 12507637, compound

Product 1

HCID 12800950HCID 12800950, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4,5-dihydro-3-(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-yl)-2(3H)-furanone (described in Example 1, 20 g, 0.074 mole) in tetrahydrofuran (200 ml) and 40% aqueous methylamine is refluxed for 24 hr. The reaction mixture is diluted with brine and extracted with diethyl ether. The organic extracts are washed with brine, dried over magnesium sulfate and evaporated. The residue is subjected to chromatography on silica gel using acetone-benzene (1:2). The eluates are evaporated and crystallized from diethyl ether-hexane to obtain isomer A (6.9 g) of the title compound, mp 169°-171° C. The eluant for the column is changed to acetone-benzene (1:1) and the eluates are evaporated followed by trituration of the residue to obtain isomer B (7.5 g) of the title compound, mp. 194°-196° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic extracts are washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe eluates are evaporated
  6. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-42520a803d8e47e891a75b597d839a97
Source dataset
uspto-grants-1979_12
Patent number
US04179503

Reaction notes

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